Ammonia → 5-Bromo-2-nitroaniline

HRID 2252061Notes

Reaction equation

HRID 2252061 reaction equation
[NH3:1].Br[C:3]1[CH:8]=[C:7]([Br:9])[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11].O>CS(C)=O>[Br:9][C:7]1[CH:6]=[CH:5][C:4]([N+:10]([O-:12])=[O:11])=[C:3]([NH2:1])[CH:8]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 123156462,4-Dibromo-1-nitrobenzene

Product 1

HCID 53147665-Bromo-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

In a sealed reaction tube, add cautiously 6 mL of an aqueous solution of ammonia (32%) to a solution of 2,4-dibromonitrobenzene (1,6 g) in 2 mL of DMSO. Stir for 18 hours at 100° C. and cool to room temperature. Pour the heterogeneous mixture into water and filter the title compound (1.1 g, 92%) as a yellow solid.

Workup

  1. customIn a sealed reaction tube
  2. temperaturecool to room temperature
  3. filtrationfilter the title compound (1.1 g, 92%) as a yellow solid

Sources & evidence

ORD record
ord-f67818b6998f4bb895edd2710c6aeff0
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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